


Taxi Driver Remix

by hjbaltimore



Category: Supernatural
Genre: Episode: s08e19 Taxi Driver, Gen, Gore, Hell, Hellhounds, Implied Castiel/Dean Winchester, Purgatory, Rescue Missions, Suicidal Thoughts, Torture, Vampires
Language: English
Status: Completed
Published: 2013-04-06
Updated: 2014-02-16
Packaged: 2017-12-07 16:15:05
Rating: Teen And Up Audiences
Warnings: Graphic Depictions Of Violence
Chapters: 7
Words: 18,665
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/750456
Author URL: https://archiveofourown.org/users/hjbaltimore/pseuds/hjbaltimore
Summary: <blockquote class="userstuff">
              <p>Sam performs the second trial on a trip through Purgatory and beyond, to save a wronged soul and deliver them unto Heaven.</p><p>Or, an attempt to fill plot holes and make the episode fit better with "Supernatural" established mythology.</p>
            </blockquote>





	1. Earth and Death

**Author's Note:**

> Warning! This contains spoilers for the entire episode of 8.19, gore, and some headcanons.

It wouldn’t be the first time he’d woken up to hurried whispers in the middle of the night. He’d be lying if he said it hadn’t gotten worse since he started taking those pep pills Dean got him, either. It was, in fact, one of the many reason’s that this was Kevin’s first bit of sleep in a couple days now, because there were only so many times you could wake up in a blind panic before simply staying awake felt like a better alternative. More often then not, they were a minor annoyances, little nagging whispers recalling all of his failings. The worst was when Channing’s voice rang sweetly in his ear, saying how much better Heaven was than being stuck on Earth with him. The only problem is, he realized as he slowly began to wake up, that the voices (or rather, voice) seemed different this time. More specific. More threatening. 

_“Kevin. **Kevin.** I know what you’re up to,”_ it growled. 

His eyes popped open and he gave shaky gasp. Crowley. 

It was nearing 2 A.M. and the only light besides the clock was an unusually bright not-quite full moon, and a single street lamp from the parking lot leaking through the thick grime and painted symbols on the house-boat windows. 

_“You’re working with them. Those Winchesters. Dead end, Kevin.”_

He sprang up. He wondered if he was hallucinating, but you're not paranoid if they really are out to get you. He stuck his head out the bedroom door, back in the room, behind the shelf-

 _“Not here.”_

Kevin really hoped he was just going crazy.

_“Not here either.”_

Under the bed-

_“Give up. I’m in your head.”_

Around the room-

_“As well as everywhere else.”_

The closet-

_“The last time you burned, me you lost a finger. Imagine what will happen this time…”_

The voice stopped. Kevin stopped too, and suddenly felt like he couldn’t move. Sweat pooled at his fingertips, and a creeping sensation as though ants were tunneling under his skin over his entire body. It all happened in less than a second, and the sensation gave way to a disgustingly numb one that made bile rise in his already too tight throat. He was almost afraid to look, but lifted his arm anyway.

Except it was gone. The hand, the wrist- all that was left an oozing bloody stump, cut clean and straight with no bone left. For half a moment he wordlessly moved his lips, unsure of whether to vomit or scream. Instead a rather loud whimper escaped his lips, only turning into a scream when he fell to the floor in a pool of his own blood, having now lost all his limbs to some unseen force. It didn’t even hurt, but in hindsight that was probably worse. With no pain to distract him, Kevin was forced to take the sight of his ragged torso, miraculously still upright in a puddle of filthy blood and tissue that smelled strongly of rotting meat. The physical sensations, or lack thereof, were dizzying, and he let out final desperate wail before falling over, unconscious.

  
\---

  
“Kevin! Open up,” Dean groaned, banging on the rusted door, “KEVIN.” 

Kevin wretched open the door right hand, heavy frying pan in his left ready swing. He didn’t care if this looked stupid or if it’d even help if a monster came charging at him, but damn if he didn’t sleep last night with anything weapon-worthy piled on his bed. He wasn’t going to stop just because Thing One and Thing Two finally decided to show up.

“Woah! Woah, geez.” 

“What’s going on? What’s with the SOS?”

“It’s him,” he huffed. 

“It’s who?”

“Crowley.”

“What about ‘im?” Dean asked, finally showing concern.

“He’s in my head.” Kevin gasped, pointing to his head.

Sam raised his eyebrow. “He’s… in your head.”

“Do you know what that means!?” he spat.

“Yeah, it means we need to up your anxiety meds.” Dean paused. “Kevin you’re dreaming. Look, if Crowley knew where you were, he’d do a hell of a lot more than mess with your head.”

“All right, where’s Garth?” Sam interjected.

“On a case… or at the dentist. I don’t know, I haven’t heard from him!”

“Okay, well what did you want to tell us that you couldn’t say on the phon- _would you put the frying pan down? Please?”_

He set it down with a clatter on the stove and sighed heavily. Turning to face the brothers, he tried to straighten himself out and stand tall. “I translated the second trial from the tablet,” he stated. Exhausted, he swept between the two to the table and picked up the translated paper from the table. 

“Y-you crazy prophet you! Good work!”

Kevin turned around and narrowed his eyes. Had they been listening at all? “If Crowley is in my head he knows!” he snapped.

“Okay he is definitely not in your head. He’s not in your head, Kevin,” they said overlapping, trying to calm him down. 

Sam raised his palms defensively. “It’s alright. We know you’re distressed. Just try to stay with us, alright?” He looked a Kevin for a moment. “What’s the second trial?”

“An innocent soul has to be rescued from hell and delivered unto heaven.”

“What?”

“’Unto.’ That- that’s how God talks.”

“Rescue a soul from hell? Like actually… go to hell?” Sam stammered, losing his demeanor. “How- how do you get a soul unto heaven? How do you even get a soul out of hell!?” He could feel himself breaking out in a sweat. He didn’t know how he didn’t see this coming, because of course- **of course** these trials would involve a trip to hell. More than ever he was glad Dean wasn’t the one doing this. It would break him. Sam well, couldn’t remember anything but a few wisps of memories from his time down under, and other than that just the hallucinations from his broken wall, but Dean never had such luck. Years ago, when he first came back and claimed he didn’t remember a thing, Sam couldn’t have been more relieved. He didn’t doubt this was the case at first anyway, but Dean remembers everything now. Still, it didn’t stop this from being any less terrifying. He tried to keep his cool.

“We’re going to need an expert,” chimed Dean.

Sam froze. That sounded a little too happy.

  
\---

  
“But first you’re going to tell us… everything.”

Sam watched Dean throw a face full of holy water in the demon’s face. Ah, so this was what that unusual enthusiasm was for. He hadn’t asked anything of Dean since they reunited, but he had a feeling that when he was looking for Castiel in Purgatory, the monsters weren’t quite as helpful as Dean had implied. It also didn’t help when Dean had insisted on taking care of Abaddon himself either, and Sam was beginning to wonder if he should…

“Unf!” the demon gasped. Blood sprayed on the floor, and the body crackled before falling limp in the bounds, and Dean wiped the blade clean on the demon’s shirt.

“All done Sammy. You okay? You kind of zoned out for a minute there.”

“Yeah. Yeah, I’m fine. You know, considering. Lets get this cleaned up.”


	2. Purgatory and Monsters

**Summary for the Chapter:**

> Ajay thinks briefly about his past, and Sam searches for Hell.

“Ajay. We need to talk to you for a sec.”

Ajay looked up from his daydream and saw the Winchesters coming towards him. He supposed he could just flit away, considering the fact that anytime a Winchester knew your name it was bad news, but he stopped. He wasn’t stupid, they about to ask for a favor. And if there was ever anyone better to have in your debt than these two, he couldn’t recall right now.

“You know my name,” Ajay said simply.

“And what you do.” Sam paused. At least, he figured it was Sam. Humans always looked too damn similar and it was hard to remember sometimes.

“We want to do business.”

“But you are mortal. Flesh and blood.” Ajay was going to make these jokers work for it. There were few things anyone ever came to an out-of-work reaper for.

“But if we wanted to cross the boarder into Hell-”

“Visitor’s pass,” Dean interrupted.

Never mind. He should have left when he had the chance. “No one wants to get into Hell,” he scoffed.

“But could a cayotaje like you do it?”

“It’s possible.” He stopped, and they both looked at him intently. “But I have special skills. I have overhead. It will be pricy,” he fished.

“How pricy?” asked Dean.

There’s what he was waiting to hear. “You two are… resourceful. One day, you will owe me a favor.”

“You say that like you know us.”

Ajay dropped his jaw a bit in disbelief. Do they even realize how infamous they are? “Of course. You’re the Winchesters.”

“Sorry. Have we met?”

“You’d be hard pressed to find someone in our business who doesn’t know you. It also helps, I suppose, that I am the one who took your friend Bobby Singer to Hell.”

Sam scoffed. “Bobby? In Hell?” he said disbelievingly, “We burned his bones. Once we did that it was over. End of story.”

Ajay gave a quick smirk. Now they’d really owe him. “Hmm… not necessarily.”

“No no no, see Bobby was on the good side of things, and good guys get the penthouse.”

“Usually. Mostly. Depends on who you know, what palms get greased. If you’re on the king of Hell’s no-fly list, no way you cruise the friendly skies.”  It was at that moment he could see the full force of the realization hit the boys.  He almost felt sorry for them.  

“Crowley,” Dean said, looking to his brother. They were quiet for a moment. “Okay,” he said finally, “lets do this. How much for two tickets down and three back?”

“Dean.”

“What?”

 _Oh God_ , thought Ajay. _Am I going to have to listen to one of their famous pissing matches?_    He sighed loudly, though he doubted either two heard him.

“Come here.”

Sam pulled Dean aside. “What the hell are you thinking?”

“You heard the guy, Bobby’s in Hell! We’re gonna spring him,” he gritted.

“We talked about this Dean, I gotta do the trials solo.”

“This is Bobby we’re talking about! And let’s face it Sam, you have not exactly been up to full speed lately, okay? We got one shot at this, we cannot miss.”

“I’m not going to miss,” Sam retorted. “I’ll bring him back.” He walked back over to Ajay. “I’m in, just me.”

He looked him up and down. “Follow me-”

“Wait wait wait. How does this… work?”

Ajay sighed again. “Not to fret. He’ll be back in exactly 24 hours time. Return for him then.”

Dean groaned. “Fine. Sammy, take this with you. It’s good luck.” He took his hatchet from Purgatory out of his coat and handed it to Sam. “Be careful little brother.”

He couldn’t look at him. He took the weapon and put it next to the demon blade in his own jacket. “Thanks Dean,” he said quietly.

Ajay and Sam left a scowling Dean at the cab. Around the corner from where he was parked was large abandoned space cover in graffiti. Ajay stared at a blue door painted on the middle of the wall, and Sam threw a confused looked him way. What, were they going to run at it like Platform 9 ¾?

“Take my hand.”

He took it, and immediately the paint began to twist and melt, eventually engulfing his entire line of sight into what Sam suspected must be what a really bad acid trip looked like. It took about half a minute, and a blinding light made him shut his eyes. It was a sensation similar to when he and Dean used astral projection in the past, and everything in his body seemed to squeeze and lurch forward. Suddenly, he hit the ground, and had to steady himself before opening his eyes.

 

 

  
\---

  
Sam’s head pounded, and it took a few seconds before the world was upright again. Looking around, it appeared to be a kind of dead, ugly forest, colors dulled to a water grey and the sky one solid, featureless sheet. Didn’t quite fit Hell, but there was a kind of uncanny valley feel to the place that convinced Sam this was definitely not Earth anymore.  
“So this is- is this Hell?” he stammered.

“Not at all. This is Purgatory.” said Ajay.

He moved his lips but nothing came out. “What do you mean this is Purgatory? This isn’t what I paid for, I booked the Hell tour!”

“Woah, woah Winchester. Detach,” he urged defensively. “This is Hell adjacent. Been down this highway many times before. We are a little under a mile from the entrance. Simply follow the stream,” he said, waving his hand towards the water to the side of them. “You’ll find a spot along it where three trees meet as one. Next to that are some rocks. There will be one in the middle with a bunch of scratches on it, but don’t worry about that. You just need to write ‘Lasciate ogne speranza, voi Ch’in rate’ on it in human blood which, lucky you, appears you have plenty of. Though you could really do it in whatever language you please. The portal really is not that picky, but I feel that Italian or Latin gives it that nice aura of mystery.”

“Are you serious?” asked Sam doubtfully.

“Dead serious,” Ajay gibed with a slight smirk.

The corner’s of Sam’s mouth twitched, but he straightened his shoulders and held onto his knife not moving.

“It’s a back door to Hell. Trust me, it will work. There really is no other way to get you there without killing you. Purgatory is the only ‘physical’ entrance.”

Sam scoffed. “Where were you two years ago when we needed this? There was a whole angelic civil war you could’ve prevented.”

“Tch. So naïve, the lot of you. And arrogant. There is a reason this is isn’t a highly advertised fact, you know. It wouldn’t have helped anyway. As I recall Crowley and the angels wanted to absorb the souls, not take a vacation with them. Visiting and interacting are two very different things, you know. Even I didn‘t know about the handy little spell that angel managed to conjure up. It takes a portal for the kind of power they needed, and only an ancient, original work of God like the Leviathan would even know the how to open it. Oh, that reminds me, you might want to look out for them on your way there and back.”

“W-wait, so you’re not coming with me?”

“Don’t be ridiculous,” Ajay chuckled. “Smuggling a mortal across the boarder is risky enough. But gate crashing a Winchester? Seriously blows. No, I’ll see you in about a third of year. Don’t worry about being exact. Just be here." He tapped his watch.

“You said 24 hours before.” Sam said, eyes widening.

“24 hours out there, sure. That’s what it’ll feel like to me and your brother. Hell is a very different place, my friend. Let’s just say, for simplicities sake, that you have 122 days. Good luck.”

Sam looked like he wanted to cry in frustration, but nodded none the less. He looked at the demon blade in his hand.

“It’s a good thing you brought that. Like I said, it’s not an easy place.”

He looked around and heard Ajay leave in a flash behind him. This was going to be a long trip.

 

 

  
\---

  
“Yo Kev, it’s me!” Dean shouted. He juggled a cardboard tray of fries and drinks in one hand and a greasy bag in the other. “Kevin.” He heard a metallic groan off to the side and turned around in time to see a somehow even more disheveled version of the prophet than before hovering behind a rusted out door. Geez, he was developing worse hygiene than Chuck had at this point.

“I believe the closet would be safest.” Kevin said shakily.

“Safe from what?” Dean asked almost teasingly.

“Crowley. He’s in my HEAD, Dean.” Dean sat the food down on the table. “And if he’s in my head he knows where I am!” Kevin gulped. “You know, we- we should move out. We’ll find another place-”

“Geez Kev. Would you chill out, huh?” Dean tried to say in his calmest, most reassuring big brother voice. “Have a burger.” He held it out like Kevin was a scared animal he had to coax out. Which in a way, he supposed wasn’t too far off. The poor kid needed to eat something. “Come on, don’t loose it on me now dude.” Kevin took a twitchy step out the door frame. “There you go, that’s it.”

“Just- tell me when this all ends. ‘Cause that’s the only thing I want to hear.”

 _Crap_ , thought Dean, It’s like trying to talk to Jimmy all over again. “No, like I told you before, this isn’t going to end.” Kevin looked up, and Dean could see huge dark circles around his eyes. “Look man, other guys, they got it easy, you know? It’s all back yard barbeques and… bowling teams. But you and me? We gotta carry a little extra weight.”

Kevin shook his head. “I can- I can’t take it.”

 _Shit._ “Yes, you can. Hey, look at me,” he growled sternly. “Now this whole thing sucks, I know. But you suck it up, and push through because that’s what we do.” Dean tried not to let his voice waver, but deep down he wondered how many times he was going to have to say this in his life. He said the same thing to Sam nearly 15 years ago. “And when you get on board with that the ride is a lot smoother.” Kevin scowled at him. “French fry?”

Kevin stuffed several in him mouth furiously, still shaking his head. “I’m going- I’m going to be in my room. Let me know when there’s a good day.” He picked up the tray and strode away to his room.

“That’s my pie…”

Kevin threw one last glare Deans way and shut the door behind him.

 

 

  
\---

  
This… this was why he went rouge. Ajay bounced happily up the street with his pizza, savoring every last greasy drop. He’d worked with human souls for thousands of years, since the first civilization sprang up (if he recalled correctly) but he now understood why they never wanted to leave their mortal bodies. Though he’d never considered taking a physical body until recently, he had to admit he’d always kind of admired humans, or even just living creatures in general for a while now. Other animals didn’t really need reapers: they, out of either ignorance, stupidity, or understanding, accepted death and could easily move on. It was these apes that were the stubborn ones. He’d heard stories about how the Australopiths were the first ones to begin insisting staying past their prime, though Ajay hadn’t existed that far back. Honestly, he had not even taken a name until a couple thousand years ago, when other reapers like Tessa began using them to make it easier to connect to those they needed to reap. He never understood why, but humans felt the need to put a name to _everything._

  
After the apocalypse, he was suppose to have been stationed elsewhere, another planet on the other end of the Milky Way. Earth wasn’t the only stubborn planet, apparently. But after it was derailed, Ajay left. There was nothing stopping him in the past, really. Death was not like God. If a reaper was somehow killed, captured, or unable to perform their duties, Death simply made another to take their place. And since humanity was apparently not going to end after all, Ajay decided it was time to see what the fuss was about. He wasn’t truly alive, seeing as he‘d chosen to posses a fresh corpse, but it was stable enough for him to pass as a regular Joe, to be seen by other humans, to eat, to sleep, to take in all the sensations that came with being alive. It was physical enough for him to die if he wasn’t careful. What exactly would happen after that was anyone’s guess. Perhaps he’d be reincarnated. There was a ritual, a whisper amongst monsters and beings like himself that could make him fully human. This body was nice but it was still rotting, albeit at a far slower pace than natural. If it was not for the wonders of gut flora living beyond it‘s host, eating would require a lot more maintenance. The ritual, which he would enlist the Winchester’s help to find, would strip him of his powers, but leave a living body in return. At least without his powers he would stop attracting demons like Crowley to intimidate him into working for them anymore. Crowley claimed to have several angel blades in his arsenal, just one of many things he claimed could kill a rouge reaper, and if that didn’t work then several others he knew could kill a regular reaper. Somehow, Ajay didn’t doubt him.

  
Spotting his cab, he got in and sat in the drivers seat. As a human, he wanted to get a job so as to attract less attention. His poor deceased vessel was a cab driver, and Ajay thought this was startlingly appropriate, considering humans often associated reapers as a kind of guide in their literature. So he took it, and made a modest living with it. If he was ever strapped for cash, well, it’s not like he _had_ to eat.

“Hello Ajay.”

Crap. He knew that voice anywhere. He nearly choked on his food, and before he could get to the door handle it was already locked. Crowley kept him from flitting away, either.

“Been a while since we chatted- too long.”

“Pizza?” he asked, voice cracking. “Extra anchovies.”

“Anything you want to get off your chest? An update?” Crowley inquired, disturbingly calm.

“Uh… no? No, not really.”

“As you recall patience isn’t one of my virtues. Well, I don’t have any virtues. But if I did, I’m certain that patience wouldn’t be one. So, you sure there’s nothing weighing on you?”  Ajay remained silent, his Adam’s apple bobbing up and down.  

“Sir, I know better than to attempt that.”

“My operative saw you leaving with Sam Winchester.”

“Oh! Oh, _Sam_ Winchester. Oh yes, that’s uh… possibility.” He could just feel his hole being dug deeper and deeper.

“You’re trying my non-patience,” Crowley hissed.

“Sir, I was just doing what I do. As you are more than aware I do occasionally moonlight as a freelancer.”

“You do not,” Crowley seethed, “ _freelance with them_. What did Sam want?”

“Well, uh, actually, it’s starting to come back. He may have wanted to get into Hell.”

Crowley was taken aback. They weren’t going to poke around Lucifer’s cage were they? No, even they weren’t that dumb. “My Hell? Why would he want to do that?”

“I don’t know. I swear, my job- I don’t ask questions.”

“And what time is Mr. Winchester due back from Hell?”

“I’m picking him up in uh, well now 17 hours. Though it really depends on whe-”

“I see,” he interrupted, “Anything else?”

He was taking this all rather well. Maybe he’ll let him go. “No.” Crowley stared. “I swear!”

“Hmm.”

For that split second he really thought he’d get off. But the next thing he knew a white how pain shot through his borrowed chest. Fuck. He should have known better than to help the Winchesters.

Crowley pulled the angel blade out, and it was covered in strings of gooey, partially coagulated blood. Huh, they really could kill reapers. “That’s one fare you won’t be collecting.”

 

\---

  
There hadn’t been anything. Not yet, at least. Sam walked as quietly and quickly as he could. There were still fallen branches, twigs, and leaves like any normal forest ground, but he still hadn’t seen a single tree with leaves actually on one. The trees didn’t even look like real trees. They were more like a crude child’s drawling of a generic tree shape, with features from all different species slapped together. Hell, there were even pine needs lying around. Nothing that even resembled a pine tree was anywhere to be seen.

Sam felt like if he were sucked into some kind of video game, it would be like this. Certain parts of Purgatory looked like a repeating pattern where someone just cut and paste the design to fill up space. Objects that did stand out seemed brighter and less dull than it surroundings. Monuments to say “no, you aren’t going in a circle”, for which Sam was eternally grateful.

  
And then the inevitable happened. He heard the snapping’s of twigs and low grunts of some unknown creature. It took a bit of struggle in his weakened state. Sam’s muscles were always aching these days, and it was harder to breathe. The thing, which he now recognized as a ghoul, shouldn’t have been able to knock him over like that, let alone knock the wind out of him. But it did, and for several minutes after beheading the thing he coughed up bloody chunks of phlegm into the stream. Sam figured at the very least if it was in the water, monsters might not be able to smell it.

There weren’t any problems after that though. Occasionally out of the corner of his eye he could catch something curious watching him from behind a tree boulder, but nothing dangerous.

There were no animals, so the only sounds besides howls and moans in the distance were his own breaths, short and loud as he struggled to make his way up a gentle slope. _Geez, when did I become asthmatic?_ He thought to himself. The air had to be thinner in Purgatory or something. No way he was getting this bad already. Also, didn’t Ajay say it was only a mile? It has to be farther than that.

He almost missed it. Doubling back a few meters, Sam saw the tree. It didn’t really look like anything out of the ordinary, at least for Purgatory. Sure it was, again, less dull than it’s surrounding, but literally anyone could walk by this and never be the wiser. He had trouble looking at it, really. His eyes kept sliding away and it took full concentration just to stay focused.

A pile of rocks, most as big as Sam was sat tightly packed together against the base of the tree, thick vines covering the writing Ajay mentioned. But like their taller cousins, the vines here were more like a vague idea of vine-ness. Dull green stems with veinless leaves sticking every which way and twisting around the trunk.

Sam cut them away with Dean’s hatchet. Scribbles on the rock were etched in mishmash of characters ranging from what looked like anything from Enochian to Cuneiform. Checking around to make sure nothing was ready to pounce, he sliced open his palm with a pained grunt and wrote “Abandon all hope, ye who enter here” in English. But just to feel smug, he used a “þ” symbol in place of the “y“.

How’s that for mysticism?

It worked, and the writing glowed blue for a moment, before crumbling away to reveal a hole like the one he jumped into Lucifer’s cage with. Before he could even think about having some horrible flash back, Sam shook his head violently and jumped in. And that’s where everything went dark. 

**Notes for the Chapter:**

> This was where I really started to change things around. Next chapter will have Sam in a much more appropriately terrifying version of Hell.


	3. Hell and Demons

**Summary for the Chapter:**

> Sam makes his way into Hell, not knowing what to expect. It turns out demons are pretty ugly, and Hell was more confusing than Heaven.

He fell through the other side, into some sort of corridor. Taking a brief look around, it looked like this would be a harder task than he first though. To mark his entrance, he left his watch on hook hanging from wall, which was crushed during his run in with the ghoul. _As if I could ever find this spot again,_ he thought to himself. With one final deep breath, Sam gripped his weapons tight, and set off.

At first he thought he was in some kind building, but in reality it was more like a street, surrounded by wall that Sam was not sure he wanted to know were made of. Looking above, there were chains and hooks crossing every which way for miles above. Ragged chunks of maggot infested flesh were tangled among them like flies on a spider web, and distant screams could be heard in-between wet thuds of bloody extremities slid off the meat hooks above. Sam remembered at one point Dean telling him about Hell in a fruitless attempt to move past the trauma. The reality was so much worse.

  
\---

  
Sam had been in Hell for about 20 days now, give or take. It was very hard to tell. Once or twice now, before silencing a demon unlucky enough to find him, they would know the time topside. He figured if 24 hours was equal to roughly 122 Hell days, than 12 minutes on Earth was about a day down here. It would have been better if his body was still on some kind of biological cycle, but he never felt more than a little grumble in his stomach, had no urge to sleep, and only needed to piss once. For minutes at time, he would catch himself not even needing to breathe, which he counted as a bonus, since even the “air” tasted foul.

Hell was nothing if not educational. For one, Sam learned that demons mostly hated each other. Hell must be far more populated than he’d seen so far, because dozens of times already he watched from afar as demons tore each other apart. He was surprised there were enough left to terrorize Earth as much as they did.

Two, a demon’s true form was more disgusting than he previously imagined, and had no idea how they could stand to look at one another. Without the hellhound glasses That were, thankfully, still in his pocket), demons looked like black smoke. With them, Sam had to will himself to hold back whatever was left in his stomach. They were gaunt, charred, grayish corpse-like figures with scabbed over eye sockets and toothless black gums, whose appearance was not even entire stable. It was like trying to look at something through rippling water, or a fun house mirror, and it make him motion sick staring too long. It wasn't even entirely clear where their bodies ended due to the smoky outlines of their skin. At least, he hoped it was skin. They didn't bleed, and hatchet while certainly intimidation did little but slow them down, but Ruby's knife still worked just as well down here as it did topside.

Three, torture was mostly done out of boredom. Some parts of Hell were more stable than other, run by master torturers and their apprentices, determined to break down still human souls in a cruel and systematized manner. But then there were small “family” groups of demons, who would grab humans just arriving and keep them in crude structures for the entertainment of demons that settled there. When they too inevitably turned into demons themselves, they would either join the group or slaughter their way out and roam the dark landscape by themselves. Though he never made it there himself, some of the demon’s claimed that the center of Hell, Crowley’s living quarters, was where the worst of the worst were kept. Instead of having the honor of join Hell’s legions as eventual demons, rumor had it they waited in an endless line in the basement of Crowley’s manor, where one song selected by Crowley himself would play non-stop for a hundred years straight before changing.

Four, Lucifer’s cage and Hell were not mutually located. While technically in the same realm, the cage was by no means accessible through Hell. Since the apocalypse, the entrance to the cage was “loose”, meaning no seals had to be broken, but to get in and out required massive amounts of power, the kind only an archangel or Horseman possessed. Or, failing that, power borrowed from the consumption of souls. Plus, there was always the chance Lucifer or Michael would beat you to the punch, exiting before the door could close. Sam became terrifyingly aware of just close a bullet they dogged when Cas pulled him out.

  
\---

  
_“Sam. Sam, wake up.”_

Sam had been wandering on the outer edges of Hell, or at least, that’s what the demon he captured told him. Hell was structured a bit like Heaven, in that while there was a centralized structure, there were also “personal” hells for the truly unique torture experience. The farther he got from the center, the more metaphysical it got. There were perpetual incoherent whispers that were driving him nuts; in his peripheral vision objects would jitter and fly apart like they couldn't decide what shape to take unless he looked; sometimes if he turned around fast enough he would see a version of himself from a few seconds ago trying to catch up.

For the first time since arriving, he felt himself getting tired. Not necessarily sleepy, but emotionally and mentally drained of energy. Physically, there was nothing different, unless finding himself in a fight with a puke inducing demon. The majority were in their corpse-like forms, but once or twice there was one with a host body, probably to receive orders from somebody else. They were the hardest to handle, mostly from guilt. He had no idea if the person inside would be trapped in hell if he killed the demon, but had no choice when they attacked. Hell was there to test him at every turn, with the demon spilling out and the first pang of true hunger in nearly three years. He’d almost forgotten what it felt like to ache for the stuff.

Moving on farther and farther out, it seemed as though light had trouble catching up to him. If he walked too fast, colors would shift and his entire field of vision would be warped, the background voices dropping to disturbingly lows tones. It became even too hard to move. Going forward meant everything turned shades blue, or even completely black, making navigation near impossible when his vision began lagging a good 4 or 5 seconds behind his feet. Around him the walls and sky bent around like he was watching through a fish eye lens.

It was too much. Sam felt like his head would split open. He ended up tripping over something he couldn’t even see, and everything slowed down as his vision went black. While he expected to hit the ground (if it could be called that), he felt his body continue to drop. He closed his eyes, and let exhaustion take his mind away, if only for a moment.

  
\---

  
“I said get up Sam.”

  
He opened his, and his heart nearly leapt to his throat. “Lucifer.”

  
“Hey buddy. Long time no see,” he simpered, “well for me, anyway. You seem to have a bit of trouble looking at me like this. Should I use Nick’s body instead?”

  
“No. No, Lucifer please.”

  
The angel shrank from his massive size. It wasn’t the first time Sam had seen his true from. While there were not many memories left from the cage, this was one he could never truly forget. The other angels weren’t lying when they said his was beautiful, if not in a conventional human way. While Cas claimed to be the size of the Chrysler building, Lucifer was at least, if not taller than the Burj Khalifa. A bright pure white body, six wings pearly white wings with light blue eyes lining the feathers- there weren’t enough languages in the world to produce the words needed to describe it. But in an instant this visage vanished, replaced with a man whose skin was tearing apart at the seams. He slammed Sam against a wall he was sure was not there a minute ago. It didn’t particularly hurt, but that didn’t make it any less terrifying either. His face was less than an inch away from Sam’s.

“I’m glad you’re back Sam. I heard you missed me upstairs! But now, we can pick up right where we left off,” he hissed.

“No. No no no. You aren’t real, you’re in the cage.”

“Yeah but you see, I heard you were in the neighborhood and what the hell, I just had to come see you! Pun fully intended, by the way.”  
Sam fell limp against the wall, falling on his knees.

“Now it seems I can’t really touch you right now,” he demonstrated, waving his hand through Sam’s face, “but we’ll fix that later. I’ve got all sorts of fun games to play in the meantime. Also, sorry to tell you, Michael couldn’t come. He had a bit of a- well, lets call it a date with your brother.”

“Adam-”

“Yeah! Adam! You know, that kid you didn’t even consider trying to release? But I’m sure he’ll understand.”

“I can’t just get him out, I’m not powerful enough!” he cried.

“Hey, you don’t have to convince me. Besides, look who else we got here.” With a snap of fingers, and a dramatic poof of white smoke, a blonde woman in pajama’s with the name Stanford plastered on it appeared next to Lucifer bound and wide eyed.

This wasn’t real. Sam tried to look away, but something kept him from turning his head or even blinking. He watched in quiet desperation as the girl’s eyes widened in terror.

“Jess…”

“Sure is!”

“Lucifer please. I’m sorry, please, just don’t.”

The worst part was, he couldn’t even flinch. Lucifer started from her scalp and, using her hair as a handle, began to peel the skin off.

“Stop it! Please!”

“Look Sam, if you’re not going to play along then just turn around and let me play by myself. Don’t ruin it for the rest of us.”

He was going to be sick. Finally managing to turn around hardly made it better. The screams were a sound he was sure he’d never get out of his head, nor the sounds of tearing and squelching as blood sprayed his back.

“Hey Sam, just ignore me. And sorry ahead of time. These darn bones keep getting in the way in the way and if I accidentally hit you with a couple of them, it’s my bad, okay?”

  
\---

  
“So then Michael was like, ‘I dunno man, I’m pretty sure the mammals aren’t making a comeback. They’ll probably die out before they get a chance to be bigger than rats again’. So then I said, ‘Look, dinosaurs are cool, but those stupid hairy things are totally going to take over if the dinos ever die off’. Anyway, long story short, I took some of my siblings and got this giant chunk of rock floating out near Mars and we tossed it into the Earth! Man, the Fate’s were pissed. Absolutely worth it though, because I was right. You mammals are so damn resilient. You‘re like… the extremophiles of post-Cambrian macro fauna.”

With a wet splat, Lucifer threw another one at Sam’s feet. For hours he had been conjuring up friends and family members to skin alive in front of Sam. He knew in his heart of hearts they weren’t real, but he couldn’t stop it either. He had mustered up the courage to run at the devil when he pulled out his mom, but fell right through the two.  
“Sorry, didn’t I mention you couldn’t touch us either?” he had gloated.

He couldn’t get farther than about ten feet either. Reaching on edge of the miserable, dark room simply made him appear instantly on the opposite side. There was a door, and Sam was pretty sure it was the exit, but if he tried to get close to it, Lucifer simply sent him flying backwards.

A lifeless, gutless Dean lay in front him like a bear skin rug, but he couldn’t even touch it if he wanted to. “I can’t do this anymore,” he whimpered. It was becoming difficult to remember why he was even here. He was going to be trapped forever if he didn’t get out soon. With one last heavy sigh, Sam fell back into unconsciousness, more tired than ever.

  
\---

  
“Sammy, you awake?”

At least it wasn’t Satan this time. Opening his eyes he was once again treated to an obnoxiously bright light, but he saw it was just the afternoon sun coming in through the shades of a nearby window.

“Dean?” he groaned. “God, my head feels awful.”

“Well yeah man, you just got back from Hell. ‘Course your head is going to hurt.”

He gave an amused scoff, and tried to get up. A jerk of his wrists said he was being held down, and he saw both hands were cuffed to the sides of the hospital bed. He looked around. It was the mental institution he and Castiel had spent time at. “Dean, what th-”

“Woah, woah man, calm down. You just got back like a day a go, take it easy. Those are there for your own protection, okay?”

“I don’t… Dean I don’t remember anything.”

“Well thank god for that, right? You’ve been screaming about Lucifer for the 18 hours. I thought you’d wake up way worse.”

“No, no I mean like, I remember being with Lucifer, but nothing after that. At least, it was an illusion of him.”

“Well it doesn’t matter now. You did it brother! The gates are closed for good.” Dean said, patting his brother on the shoulder.

“Just like that?” he asked skeptically. “There was nothing else to do?”

“Nope. We can finally move on in our lives. Well, I’ll be seeing you bro. Maybe in a month or two, if I’m in the area.”

“What.” Sam asked with an edge of panic and anger in his tone.

“Look, I’m glad to have you back, but your noggin is fried after that last trial. You need to stay here for a while.”

“Dean- Jesus I’m fine. I just need some sleep. Get me out of here. Do not leave me here Dean.”

Dean sighed. “Sam…” He sat back down, and looked his brother in the eye with a complete lack of sincerity. “I’m done with you. You are probably going to be nuts the rest of your life, and I am done taking care of you. I’ve been doing it since you were born, and I am done dealing with your screw ups.”

“Dean what the hell!? I didn’t do anything wrong.”

“Oh yeah? Because I seem to remember you leaving me to die in Purgatory. So now, I’m leaving you to die in this god forsaken loony bin.”

Sam sucked in a deep breath. Was this real? The Lucifer thing was bad, but at least he knew it was some torture Hell had conjured up for him. This, he wasn’t so sure. “Dean, you don’t need to take care of me. Just sign me out of here.”

“No frickin’ way. You’ll just ruin it.”

“Ruin what?”

“Look Sam, I thought I needed you, but truth is I don’t. I got Cas now, and despite everything, he’s let me down way less than you. He’s more family than you’ll ever be.”

“Dean-”

“Let me finish. Benny? Kevin? Charlie? Linda? Garth? They’re all I need. They’re my new family, and it doesn’t include you, you blood sucking freak. You’re more of a vampire than Benny is at this point. And I only got rid of him because of you.”

“Dean, not you. I swear I haven't done that. I wanted to but I didn't drink any I swear. You can’t say this to me man. Whatever it is I’ll make up for it, please!”

“Shut up!” he yelled.

Sam flinched, He expected a hit.

“If you’re so worried, get your girlfriend to bust you out. Oh wait, she found someone better.” Dean spat, heading towards the door.

“No. Nononono Dean please don’t leave me here again!” he shouted at his brother. No, not again. He couldn’t handle being in this place again. He really was going to die here, wasn’t he?

“Oh please, shut up.”

Sam looked around. The room began to melt away, and with it his bondage. There was nothing there in the first place, and he found himself lying on the ground as a rotting, filthy hand grasped at his chest. Sam was back “outside”, wherever in Hell that was. A waxy grey body stood over him and smirked.

“Wow, when a friend of mine said he trapped a Winchester down here, I thought he was crazy. Turns out it’s my lucky day, Sam.”

**Notes for the Chapter:**

> Okay so I lied about the chapter coming out on Friday. I went through 4 rewrites and I'm still not really satisfied but it was getting too long, also I have homework to do. Thanks for reading and let me know what you think.


	4. Sufferings

**Summary for the Chapter:**

> Sam finds himself stuck with a demon that wants a ride out of Hell. What's the worst that could happen?

**Notes for the Chapter:**

> Warnings of body horror and raging Destiel subtext.

Before he even had time to blink, the demon had grabbed his forearm and Sam found himself in some sort of dungeon. Grey stone, no windows, but a rather sinister looking metal cage door.

 

“Don’t bother,” it warned.  “You’d never find your way out.  Now sit.”

 

He felt himself forced down on a large, bed sized board standing at an angle.  Hands and ankles strapped down and crudely cut metal around his neck, he knew there was no waking up from this one, and the demon’s putrid breath came down on him less than an inch away.

 

“Something wrong?”

 

“Yeah, you make me want to puke,” Sam retorted with a groan.  It clenched it’s hand and his stomach was crushed with an audible squelch.  He wanted to scream. All he could manage was a quiet whimper. He really hoped the stupid hell hound glasses would just fall off and break at this point.

 

“How about now?”

 

He gagged up a mouth full of brown blood.

 

“You are something else, Sam Winchester. You may have that nice little meat suit to cover it up topside, but you can’t hide it here.  Your soul is truly the most hideous thing I’ve ever seen.  I’m not even sure you’re still human.  You look more like a… charred lump of bloody hamburger.  Words don’t really do it justice, though.”  

 

The demon cupped Sam’s face with his hand examining and stretching his facial skin, eventually recoiling in disgust.  “Tell me Sam, why shouldn’t I just kill you, or turn you in to Crowley right now?”

 

He closed his eyes.  It was becoming harder to breathe, and he felt the metal cutting into neck, to afraid to turn his head to much for fear of slicing his jugular.  “Look,” he gasped, “you would have already done it if you didn’t want something.  Just let me out of this and we can talk.”

 

It smiled. Or something. The light was actually good enough for Sam to see through his half open eyes into the demon’s toothless mouth.  Beyond the black, slimy tongue was, well, nothing.  Instead of a throat was flap of skin stretched over the back of the mouth like a drum.  

 

“You caught me. I need a little help.”

 

The cuffs clicked open and Sam fell to his knees, massaging his throat a bruise started to form.  

 

There was no way the demon was this dumb right?  He whipped the demon knife out of his pocket and swung at the thing.  He fell right through, and his whole body convulsed in an incredibly unsettling, not unlike the time he was given an electroshock “treatment“ back at the mental hospital.  He fell on his back, and with a small gasp he saw thin, bright green vines worming their way out through the pores on his arm.

 

It leer over him. “I’m not fooling around, Winchester. Either shut up and cooperate, or become living pile of fertilizer.”

 

Sam felt something tickling his throat, and an awful itchy sensation and pressure behind his eyes.  Lifting a trembling hand to his face he felt more of the plant sliding out slick with saline from his tear ducts.

 

“Stop it.  Stop it, please!” he pleaded, panicking.  He couldn’t help it, he tore at his skin but the vines grew faster, splitting his skin with a white hot pain.  If this lasted any longer, he was going to die, he just knew it.  Or, if he was really unlucky, he wouldn’t.  Sam dropped the knife, holding what was left of his hands to his eyes to keep them from popping out of their sockets.  Somewhere off to the side, he heard quick snap,and the vines were gone.

 

“You’re pathetic.  Worse than your brother.  Now, are you going to listen or should I persuade you more?”

 

He took a deep breath, trying to stand of wobbling legs. “What do you want?”

 

“I don’t know if you’ve noticed,” it said, pacing in front of the door, “but Hell is not exactly the easiest place to get around in, which of course makes me wonder: how in the world did you get in?” It paced around behind Sam, who didn’t dare to turn around.  “But then I thought ‘well clearly he must have an exit plan, what does it matter how’.”

 

Sam stared.  “You… need a ride out?”

 

“Bingo.  You really are the smarter one.”

 

“You can’t just, I don’t know, fly out or whatever?”

 

“I  take back what I said.  No, I cannot.  Occasionally spots in this lovely world of ours will weaken and we can slip right through, but those can happen anywhere at any time, and Hell is a very big place.  I’ve never been that lucky.  Sometimes an idiot will summon you, but that’s very rare. To do it alone you need power, raw power to claw your way out of here.  Sometimes help from a more powerful demon.  I’m pretty short on friends in high places as of late, and well… long story short, give me a ride and I won’t kill you.”

 

“Uh huh.”

 

“I mean, I suppose it’s possible you are the quicker draw and could catch me off guard, kill me. You could continue wandering around Hell to finish doing… whatever it is you’re here for, with no direction.”

 

Sam rubbed his jaw and snorted. “Fine, it’s a deal. I need to find Bobby Singer. I don’t suppose you just happen to know where to find him?”

 

The demon plucked Ruby’s blade from his hand. “Just for a little security,” it reassured,  “and no, I don’t, but I’m certain there is someone around who will.”

 

\---

He’d never admit it, but cooking had always been a very soothing activity for Dean. Not like, he’d become a chef or something, but like as a hobby. And since he couldn’t remember the last time he’d been so nervous (well he could,but that’s not the point), he was thankful to have someone to cook for, since Cas was on the lam and Sam was visiting Hell.

 

“Hey, Kevin! Come in here and grab some of these eggs.” No response. “Kev! Come on, man. You can't hide in there forever.”

 

The main door creaked open and very tired, slightly dirtier Kevin slouched in.

 

“Where the hell you been? What happened to being scared?” Dean dumped the contents of the pan onto a plate and handed it Kevin.

 

“I am scared. So I made a preemptive move.”

 

“So... wait, made a what now?”

 

“I can't sit here with the tablet like a- like a sitting duck a-and Crowley breathing down my ass. Getting rid of the tablet just takes off some of the pressure.”

 

Dean dropped the spatula. “Wait. Getting rid of it?”

 

Kevin held up his free hand defensively. “Temporarily. I hid it.”

 

“What? Where!?”

 

“If I tell you where, it's not hidden, is it?”

 

“Kevin, tell me where the damn tablet is, or I swear to you-”

 

“You'll what, Dean?” Kevin said, slipping backwards into his overly-sigiled room. The door closed with a hollow thump.

 

“Kevin!” He yelled, pounding on the door.

 

“Kids. So cute when they're little. Then they turn into teenagers, and the party's over.”

 

Dean turned his body so fast he nearly flipped the table he was standing next to. He opened his mouth to say something, but there were too many obscenities he wanted to shout at once that he just ended up scowled.

 

Naomi extended her hand. “We haven't been formally introduced, Dean. My name is Naomi.” She tilted her head, a gesture Dean had to wonder was just some angel thing, because every one he’d ever met did the same thing when either confused or being a condescending little shit. He backed up.

 

“Oh, I know who you are. And I know what you did to Cas after he got out of Purgatory.”

 

“After I rescued him from Purgatory, you mean,” she corrected in a sickeningly sweet tone, “at the cost of many other angels' lives, I might add.”

 

“You screwed with his head and had him spy on us.”

 

She finally put her hand down, smoothing the sides of her vessel’s grey suit. “Well, it is true that I have spoken with Castiel many times, trying to reach out to him, trying to help him. Dean, you must have noticed how Purgatory changed him. I mean, he's been unstable in the past, but I was shocked at how damaged he is now.”

 

His lip twitched. “Stop, okay? Don't- don't try to spin this. You think I don't know that you told him to try and kill me?” His stomach dropped. She certainly wasn't wrong so far.

 

“Hmm. Yeah, I suppose that is how he would hear it. When I learned of the Angel tablet, I did tell Castiel to get it at any cost. That's my job- to protect heaven. I'm a warrior, just as you are. What would you expect? And now Castiel is in the wind with a hydrogen bomb in his pocket, and I- I'm scared, for all of us.”

“Save it. See, I don't trust Angels, which means I don't trust you.” He spat.

 

“And yet you haven't warded this place against us.”

 

An agonizing jolt in the pit of stomach made Dean lose his balance. His damn face betrayed him, and the subtle hint of a smile rested on Naomi's lips.

 

“I know. You're hoping Castiel will return to you,” she said, beginning to pace. “I admire your loyalty. I only wish he felt the same way. I know you don't want to believe it, Dean, but we're on the same side- shutting the Gates of Hell, bringing Castiel in from the cold. Take a moment. Think about what I've said.”

 

He didn’t know how to respond. He was vaguely aware that he hadn't take a breath in several seconds now.

 

“Oh. I know you've been doing business with Ajay. He did mention, didn't he, that his way into Hell is through Purgatory? I knew you'd want to know. You see, we can be of help to each other.”

 

And just like that, she was gone.

 

His entire body shook. He yelled, screaming nonsense and grunting throwing whatever wasn't nailed down against the wall. Anything was better than breaking down in tears, which is what Dean felt like he’d do if he stopped.

 

From behind the door, Kevin cringed at the muffled bangs and shouting. He clutched at the filthy pillow he’d been sleeping on, and tried to cover his ears.

 

**Notes for the Chapter:**

> I'M NOT DEAD!
> 
> You guys won't believe what happened, but my old laptop literally went up in flames, taking all the chapters I wrote for this fic with it. So then I had to buy a new computer, and now I'm retyping all the last chapters.
> 
> Let me know of any errors you find, and I promise this will be finished in the next week.


	5. Anger and Escape

**Summary for the Chapter:**

> Sam springs Bobby. Dean gets a slightly less pleasant surprise.

**Notes for the Chapter:**

> Warnings of head canons, time skips, homoerotic undertones, and poor editing.

It took nearly another week wandering around Hell to get to Bobby. At least, thats what it felt like. Most of the time was spent hacking their way through groups of demons in their path, and the rest having to avoid the more dangerous parts of the “landscape”. Eventually, they ended up doubling back around to area he came in, not that he told the demon. He was still hoping he could weasel out their deal, and didn’t want it knowing about the exit in case it decided Sam was finally expendable. He wasn't complaining, though. After all, he needed to go out the way he came in (assumably, anyway, seeing as Ajay dumped Sam off before he could ask), and walking past his watch, still placed where he’d left it, reassured him of his mission, which was becoming more and more tempting to simply abandon with each step.

 

When there was no present danger, Sam tried to keep himself occupied, asking about the mechanics of Hell.

 

“How the fuck should I know any of this?”

 

“You’re a demon. I just thought you might know a little about the place.”

 

“I’m pretty sure as a human I was never physicist. Dying doesn’t make you any smarter. I don’t fucking know why the speed of light is slower in some parts than others, or whether Hell has an edge, or why Crowley decided to turn his headquarters into the afterlife’s version of the DMV. And frankly, _I don’t care_.”

 

Sam couldn’t help but smirk at the fact he just might be able to annoy a demon to death, though he himself was getting unfathomably irritated. “I’m just trying to pass the time, of which I am quickly running out of. If I can’t get to my friend in time, it won’t be my fault if I’m forced to leave before you can jump ship.”

 

Suddenly it stopped walking. They were in a cramped ally of (houses? they kind of looked like houses)  one-story buildings slapped together with trash and compacted viscira. The demon pushed Sam through the nearest archway. It stood over Sam, who had fallen flat on his back.

 

“How about I tell you what I _do_ know,” it hissed. “Once upon a time, there was an idiot named Dean Winchester, who was dragged to Hell thanks to piss poor self esteem and an inability to learn from other’s mistakes. He spent 29 years and 364 days yelling one name, until he could no longer remember why, or what they even looked like. On the 30th anniversary of his descent, he picked up a rusty blade and carved that name into his first victim’s chest, before hacking them to bits. The entire time, tears streamed down his face as he cursed the name he’d given his life for. The end.”

 

He didn’t know what to say, but getting back on his feet felt like an impossible task.

 

“Tch. Stupid meatsack. Stay here, I need to get some information.” It turned to leave.

 

“Yeah, and leave me here defenseless? I don’t think so. Either give me the knife back, or I’m coming with you.”

 

“I’m going to get information on your stupid friend’s whereabouts so that I can get the fuck out of here. Do you really want to waste precious time arguing?”

 

“Yes,” he said, struggling to stand back up, “I do, actually. I have been down here for at least two months. I’m _tired_. And weak. If you don’t give me a weapon, and some other demon finds me, I don’t know if I’ll have the energy to fight and win. I’ve got no choice but to let you lead me around, so you are just going to have to trust me to not kill you.”

 

It grunted, taking the blade and throwing it at Sam’s feet.

 

“Don’t. Move. I will be back within the hour.”

 

Sam breathed a sigh of relief. He’d worked with demons more times than he could count, but it never felt any less dirty. Nor had he ever had to spend so much of an extended period of time with one before.

 

Well, maybe except for Ruby. Or any of Azazel’s lackies he’d unknowingly befriended growing up.

 

He slowly sat himself back on the ground. Hell was dark, but through the power of some unknown, dim red light source, was rarely pitch black. It was only when the light was slower than his walking pace did it become dark. He couldn’t even close his eyes to block it out. Like pretty much everything else, shade and shadows didn’t seem to work quite right down here.

 

He stroked and examined Ruby’s blade. He wondered if she really meant all those words of encouragements, even those seconds before he was forced to kill her. Did she love him? Could demons feel love?

 

Meg had implied as much before her own death. Sam supposed that if a demon could have any semblance of love for an angel of all things, then perhaps Ruby could have… well, it didn’t really matter now, did it?

 

\---

 

“It’s not too far now. I have it on good faith that there’s a lovely little torture center just a small walk from here.”

 

“That way?” asked Sam.

 

“Yes that way.”

 

“Okay, but that is literally a river of a blood. And there are hellhounds guarding the shore.”

 

The demon gave off the most unsettling, guttural chuckle he’d ever heard. “Indeed, I suppose so. I wouldn’t worry about it. They don’t attack demons unless ordered to by their handlers, or if you threaten them. They’re just there to keep the human souls from running off before they’ve become demons themselves.”

 

“ **I’m** a human soul.”

 

“Trust me, you don’t look it. Remember what I said a while back? The whole hamburger thing?”

 

“What about my body? Are you trying to tell me they won’t notice it?”

 

“They only see souls and spirits and such. Bodies sometimes just happen to be in the way of getting to the average soul, is all.”

 

“How comforting.”

 

“Just get across the bridge. And try not to make eye contact with anything. It’ll go much faster if they aren’t screaming at you. I’ll wait on the other side. All this walking is exhausting. I don’t know how you mortals do it all the time.” It paused, and smiled cruelly. “If it helps, everyone in there is a murderer. Innocent souls need far more work than perpetually boiling to death.”

 

In an instant he vanished, and Sam made his way down a shallow cliff. Beyond the river, if it could even be called that, was flat land as far as he could see. Instead of any more mountains or hills or god forbid another forest (he will never unsee what is saw in that “forest”), the land was covered with rather foreboding structures. The chains that filled the sky were dipped much lower, with some even anchored there, making for a revolting sight of gore sliding off hooks and falling like rain to the ground.

 

He tried not to look, he really did. The worst part was the heat it gave off. _Thank goodness, of all the scientific laws broken in this horrible, metaphysical realm, at least convection currents still worked,_ he thought bitterly to himself.

 

Lucifer once told him he preferred the cold. A distant, not-quite-memory bubbled to edge of his mind, of unimaginable terror at the hands of an ice cold monster. Castiel had saved him, absorbing the memories of his time spent in the cage, but at the cost of prolonged feelings of presque vu whenever the subject arose. Apparently the demons never got the memo about their creator’s preferred climate.

 

\---

 

Getting to Bobby after the river was all a blur as he continued to try and block out the screaming souls reaching and crying out to him from behind bars. Unlike the ones in the river, these were all people who had made deals with cross-road demons. For that reason alone, he felt himself losing resolve.

 

The building they were in looked kind of like a jail, except each room contained only one person, with everything and anything that could be used to inflict pain laying in piles wherever there was even an inch of free space.

 

“Fun fact, Winchester: this place? Used to be Alastair’s. This building in particular was to break down the average deal maker, but there is a mansion next door where he kept his favorite projects. He lived like a king, being Hell’s top torturer. You should've seen your brother’s room…”

 

Sam slammed the demon against the wall. It felt like he was trying to hold up a jittery bag of ground meat. It was nauseating. “Shut up. Shut. Up. I don’t want to hear any more about my brother’s time down here, you stupid piece of filth. At this point, I could make it the rest of the way by myself, so don’t test me,” he spat. “And if I find out this was all a trick and Bobby Singer isn’t here, I will slice you into strips and feed them to the hellhounds. Got it?”

 

It was silent, making no move against him. Sam let it go, dropping the demon to the floor.

 

“What a waste of potential.  You really were Lucifer’s true vessel. Such a waste,” it whispered.

 

Sam didn’t bother waiting for the demon to get back up. He kept moving, checking each barred window for a familiar face when suddenly, he found one with none at all.

 

It was a room bigger as the rest, yet had no door. Just an empty doorway, and a man sitting on a slab of stone, face away.

 

“Bobby?”

 

\---

 

Dean was pissed. Beyond pissed. He didn’t want to admit it, but Naomi had wormed her way into his head against all gut instincts telling him not to believe a word that came out of her stolen mouth.

 

He was on his way to meet Ajay. Sam wasn’t due back for another couple hours, but anything was better than sticking around Garth’s boat and having to face Kevin. There was no way he hadn’t heard the whole thing with Naomi from his safe room. And Kevin, bless his heart, would probably ask if Dean wanted to talk about it. There would only have been two outcomes from that: either he’d have spill his guts and give the kid something else to worry about, or he would’ve flipped his shit. Neither were desirable situations to responsible for.

 

Dean turned into an alleyway behind a row of buildings, leaned against a brick wall and slid down, stopping just short of a suspiciously smelly puddle.

 

“Cas?” he began, looking up to the cloudy sky. “Cas, I’m pretty sure you can still hear me I- I really need someone right now man. Sammy’s in Hell. I tried to stop him, honest to God I did. He… he’s definitely strong, you know? But it’s…”

 

He choked down some hot tears he could feel welling up.

 

“I don’t uh- I don’t think he was fully prepared to go down there. It should’ve been me. At the very least I should’ve reminded him of the whole time thing. He’ll have been down there for months. God, what he’s going to see there… How can I possibly forgive myself for that, Cas? I let him go to Hell again. What are we even doing?”

 

He had stood up, walking back and forth between a chain link fence and the brick wall.

 

“What if he doesn't make it? Sammy will have given his life for this stupid world all over, only this time I’ll have no one left. I can’t protect Kevin by myself forever. Bobby, Lisa, Jo and Ellen, Pamela, Dad… and now you!” He kicked over a trash can, smashing a hole through the plastic with the heel of his shoe.

 

**“Don’t you get it you stupid bastard? You left me here alone! Why do you always leave me!?”**

 

He grabbed the fence and steadied himself, breathing hard and fast. He wanted to punch something, some _one_.

 

“But you won’t come. Either because you aren’t listening, or just don’t trust me that much.”

 

He almost expected to hear wings rustling, followed by a “hello Dean”, or at the very least someone running out to tell him to shut up. He didn’t bother to stick around though, and when he finally felt himself calm enough to not break down in front of Ajay, he turned back on to the main sidewalk and made his way down the block to the parking lot where the reaper said he’d wait.

 

“Ajay! AJAY!”

 

Dean pounded on the window. It was hard to see through, with rainwater obscuring the glass along with the steamed up windows. He tried for the handle, which was unlocked.

 

“Ajay, come on dude I-”

 

With wet thud the body fell to the ground at Dean’s feet.

 

\---

 

Bobby turned around slowly. He never seemed “old” to Sam when he was living, but ironically, now that was dead, his age truly showed.

 

Bobby sighed. “Hello Sam,” he said quietly, and without emotion.

 

“Jesus Bobby, you have no idea how glad I am to see you.”

 

Sam ran at him, throwing his arms around the other man, squeezing hard and shaking a little. Bobby didn’t move, didn’t react in the least. If Sam had noticed, he didn’t care.

 

“I’ll explain everything later, just come on, we got to run for now. And uh,” he looked at his demon companion waiting impatiently at the entrance, “Don’t worry about that for now, just follow me.” Sam grabbed his hand,raising an eyebrow when he didn’t follow.

 

“I thought you guys were done with this schtick. You’re running out of ways to make it believable.”

 

Oh. He got it it now. “No Bobby, listen. I’m not a demon, or a hallucination for some torture, okay? I’m really here, and we really need to move, so come on!” He said, yanking his arm with all the strength he could muster.

 

“Yeah yeah. I know the drill. Alright, how far are we going this time? Will we at least get out of the building before we get 'stopped'? Because if not I’d rather just stay here and get on with it.”

 

“Bobby, it’s me, Sam. Get the fuck up and move. I don’t care who you think I am, get up!”

“We got company!” said the demon, before moving out of the way, letting two mooks come straight at him.

 

“Shit!” Sam hunched down, smashing one them into the wall with it’s own momentum, and stabbed it through the back of it’s scaly neck with one swift motion. He turned to the other one, blood thirst in his eyes, while the other grunt demon stared in what could only be described as abject terror.

 

“Winchester. What the fuck are doing here!” It shouted. It turned to run, but Sam stabbed in the spine and it fell where it stood, crackling and sizzling until it dissipated in a faint black cloud.

 

His companion laughed, before turning his sunken face back at Sam, totally serious. “They won’t all be idiots like that, you know. Drag this guy by his hair if you have to. Let’s move!”

 

Sam yanked Bobby’s arm again, and this time it moved with him. The three ran out, past several demons summoned by some alarm. With those he could, Sam barreled right through. With others that refused to budge, he slashed at with the knife and kept going, without bothering to check if they followed.

 

“Where are we going?” the Demon asked.

 

“Remember those streets with the empty houses? The exit is along one of them, we just have to run through!”

 

After about an hour, when Sam had decide there was no one still following them, they walked up and down the cramped streets of gore strewn huts.

 

“I’ve got admit, you guys are really committed to this,” said Bobby.

 

Sam sighed. “I know, Bobby. I’ll convince you eventually it’s me, but for now, let me know if you see a watch okay? It’s around here somewhere, and it marks our way out.” Sam smiled sadly at Bobby, trying to look his sincerest.

 

“Well, it’s a new one, I’ll give it that,” he mumbled.

 

“Got it!”

 

It was an innocent enough door, it weren’t for the fact that this was the _only_ door Sam had seen on any of these houses. Like back in Purgatory, it took at his concentration to keep his eyes on it, like the door itself actively didn’t want to be seen. “Just follow me.”

 

Unlike coming in, going through the portal this time wasn’t suffocating. On the contrary it cool, almost soothing if it didn’t feel like is was sucking all the air out of his lungs. He fell gasping and wheezing on the other side, to a small pit surrounded by vibrant rocks. He climbed out and put his watch back, looking as Bobby and the demon joined him. Bobby looked the same (except washed out in dull, grey toned colors), but the demon just looked more horrifying, if possible. Instead of being fuzzy around the edges, blending into the air, it was fully solid, making every nauseating detail of it’s gaunt body sharper and more exaggerated.

 

“What is this place?” Bobby asked in amazement.

 

“All right, don't get all pissed off,” he replied defensively, more to the demon than to Bobby.  “It’s Purgatory.”

 

It took less than a blink to find himself pinned to the ground by the demon, gnashing it’s near toothless mouth and claws at his throat. “ _You think you can trick me? Leading me to Purgatory to ripped apart by monsters!?”_ it screeched.

 

“I will ride your lifeless skin out of this place, and slaughter your stupid brother. You want to know what Alastair’s favorite student did for ten years? He made me, and hundreds of others like me. Tortured me until I left any semblance of humanity behind. And then what? He gets a free ride out by angels and a new body, while I was left to rot and become this?”

 

It sliced his shoulder, blood gushing from the wound as he struggled to keep the demon from grabbing his neck.

 

“Why don’t you Winchesters just STAY DEAD-”

 

The tip of the knife had pierced the skin covering the back of the demon’s throat, the whole body crackling and disintegrating like the others in Hell, until it was nothing but a black wisp. Bobby slowly, shakily moved the blade away from what was now Sam's chest, eyes wide and breathing heavily. He held out his hand and helped Sam to his feet.

 

“Sam, is that really you?” he asked in disbelief.

  
He held a part of his sleeve that had ripped off to the wound, blood soaking through and staining his hand. “Bobby first, I need help. Then, I think I owe you some catching up”.

**Notes for the Chapter:**

> Not much further now! The next update will be the last, though I might end up splitting in to two chapters. I'd expect it up within the next three days.


	6. Prayers Favors and Blood Flavors

**Summary for the Chapter:**

> Bobby is just thankful to be anywhere that isn't Hell, and Dean wins worst best-friend of the year award.

**Notes for the Chapter:**

> Warnings of vaguely suicidal thoughts and lightly implied human/angel smooches.

Dean tossed the empty bottled between his hands. He’d been better about alcohol habits as of late, but today felt like a damn good day to make an exception. Not like he could get drunk anyway, off a single bottle of light beer no less.

 

He’d called Benny three hours ago, who said it would take him at least four to meet up with where Dean was now. He wondered if Sam had noticed Ajay wasn't coming yet.

 

If he wasn't dead already, that is.

 

He had spent the past few hours trying to find ways of making himself busy, first by disposing of Ajay’s vessel. The smell was atrocious, and had to have been dead for way longer than when Ajay was actually killed.

 

Now sitting in the Impala, he watched raindrops slide down the windshield, still nervously playing with the bottle.

 

He was probably the worst friend to exist. He couldn’t believe Benny didn’t hang up on him, let alone agree to come and meet him for the sole purpose of being beheaded to save someone who hated him.

 

“It is so good to hear your voice Dean. I mean it.”

 

An uncomfortable laughter rose in his throat. “How-how you been?”

 

“Oh, you know... I get by.” The strain was audible over the shaky cell connection.

 

“I guess I let you down, huh?”

 

Benny gave his own nervous laugh. “Look I’m… uh, I’m just happy to hear from you.”

 

“You might change your mind about that.”

 

“Why, what do you mean?”

 

“Benny, I got a favor to ask you. And it’s a big one.”

 

\---

 

Benny had tried. He’d really tried.

 

It had been pretty easy to adapt to the modern world. It had been only 50 years, after all. Cell phones were a blessing, and the internet? Last he’d heard it was some military thing. Now it was amazing. It was impossible to be bored from it.

 

It was things that hadn’t changed, that were the hardest. For example, humans. Everywhere. Just… everywhere. Way more than before. It was impossible to get away from the temptation. Taking donated blood helped, but it was no substitute. Especially since it had to be kept cold. There was nothing worse than having cold blood. It was having cold soup; just because it’s edible doesn’t mean you want to eat it that way.

 

He’d never admit it to Dean, but the night he’d ripped open that hunter’s throat was the happiest he’d been since he’d got back. Well, it was less pleasant once he saw the horrified look on his great-granddaughter's face. He had intended to reveal himself to her one day. She had the same eyes as her great-grandmother. He wanted to tell her that, tell her about their family. Instead he left her there, confused and standing over man clutching at the hole where his vocal cords used to be.

 

Benny sat on the couch and put his head in his hands.

 

It didn’t feel real, none of it. He almost wished he was back in Purgatory, slashing his way through back to back with Dean, who was probably one of the only decent friends he’d ever had since he’d left humanity behind. When he and Dean had first teamed up the guy barely talked, but once you earned his trust he never shut up. Benny found it weirdly endearing, especially after only having monsters with grudges and temper issues to talk to for five decades.

 

Dean hadn’t told him what the favor he was asking was, but Benny had gut feeling. It probably had something to do with his brother. Whatever it was, it had to be better than sitting here in this miserable motel room.

 

“What is it Dean, are you in trouble? You need some vampire to come save your sorry hide?” he’d chuckled.

 

The other end was silent, trying to find the words. “Well, it’s just… I can’t say. You might not come. I want to ask you face to face.”

 

“Dean, there ain’t nothing you can ask of me that I’d refuse.”

 

\---

 

It had been about 200 years, give or take, since he’d seen his boys. The only reason he could even remember who they (or anyone important to him for that matter) were was ironically thanks to the demons. Bobby was ashamed to say that no matter how many times it happened, there was always a small glimmer of hope bury deep in his soul that yes, the Winchesters had come for him! They discovered he was in Hell, and came to rescue him! Of course, the first few times it happened, he fell for it hook, line, and sinker.

 

If his demonic wardens really wanted to hit home, they would simply tell stories of Alistair's greatest apprentice, or rumors of the tortures that Lucifer had invented over his eons of incarceration, and the two men he had in his possession to test them on. But really, Sam and Dean weren’t even the most common apparitions. 

 

His wife Karen seemed to be their favorite, especially since they didn’t have to pretend anything. A demon would simply slip into her skin and scream at him until his eardrums shattered, all too happily reminding him that he was the one who killed her in the first place. Bobby didn’t need to believe it was really her for the guilt to eat at him.

 

Once, they set loose a hellhound that looked like his old dog Rumsfeld. It made him wish he’d had time to mourn his poor dog while he was still alive. Even when it began chewing on his intestines while he was forced to watch, he couldn't find it in himself to hate these creatures. They were never used against him again.

 

All his old friends and acquaintances made an appearance at least once to psychologically torture him. It all ended the same, with their bodies beginning to ooze black blood from every orifice, smiling and crying and demanding to know why he got to live so long, when theirs were cut so short. Castiel too had appeared many times to him in this way, splattering Leviathan blood every which way, except that he would go one step farther, with a Glasgow smile that seemed to extend past the corners of his face as his smashed Sam’s head like a pumpkin, and devour Dean in a way so perverse, Hannibal Lecter would squirm.

 

Bobby watched the world in slow motion as the demon he stabbed disappeared from existence. He should be one of those things by now. Yet in another twist of irony, it was Crowley, the one who who order him to be dragged down in the first place, that kept him human.

 

“You morons!” he had screeched one day. “I don’t want that bastard to be a demon! He doesn't get that privilege. You are to keep him human until I say so. If that means you have to be a little less physical with the torture, then fine! Idiots!”

 

And yet, here they were. He prayed John, wherever that poor bastard was, couldn’t see his thoughts, because the first word that came to mind was “ _son_ ”. _My boy came for me after all, it’s the real deal this time._

 

He wrapped up in a bear hug. “Jesus, Sam…”

 

“Ow! Ah, Bobby, I’m glad to see you too but-”

 

Bobby pulled back, with his own sleeve now sticky with blood. “Sorry boy, here,” he ripped off the rest of Sam’s sleeve and knotted it tightly around the wound.

 

Sam looked at Bobby and smiled. He looked the same as the day he died, maybe a little bit older, if that made any sense.

 

“How… why are you here?”

 

“Dean and I we’re- we’re going to seal up Hell?”

 

“What does that mean?”

 

“Something about the ‘Gates of Hell’. Basically we’re shutting the gates, so that no demons can get in or out. Forever.”

 

“Sounds pretty good to me. What’s the catch?”

 

“I have to go through three trials that Kevin translated from the tablet.”

 

“Who?”

 

“Oh uh, I don’t remember if you ever got to meet him before you uh, _moved on_ , but he’s a prophet. He translated the Leviathan, and now the Demon tablet for us. He’s just a kid but, he hasn't let us down. You’d have liked him.” Sam cleared his throat. “Well anyway, the second trial was to rescue an innocent soul from Hell and deliver them to Heaven. That’s you, by the way.”

 

“Well damn, I just won the lottery, huh? Though you seemed to have stopped a little short.”

 

“That’s the thing, the reaper who showed me in should be here really soon to get us.”

 

“How soon?”

 

“I’m not entirely sure. He said exactly 24 hours to Dean, but I’ve been down there for months, so I can’t tell how much time it is. It shouldn’t be more than a couple of hours… unless we missed him all together.”

 

Bobby’s eyes got wide.

 

“But Dean wouldn’t let that happen!” he reassured. “He’s up there taking care of everything! We just need to wa-”

 

They heard a low growl, followed but an ungodly screech in the distance.

 

“Isn’t this where the leviathan are?” Bobby whispered.

 

Sam heard a noise above him and jumped, knife pointed out for defense. “We should move.”

 

\---

 

“If you want nothing to do with this, I completely understand.” Dean was leaning against the Impala. Or attempting to. He couldn't seem to get comfortable, and just ended up awkwardly lying against it, trying to keep his knees from giving out. He wasn't sure if it was because he hadn't eaten or slept for the past two days, or nerves from asking a blood-sucking monster who just happened to also be his friend, if he could behead him.

 

“Wow. When Dean Winchester asks for a favor, he's not screwing around.” There was that nervous laughter again. Dean winced.

 

“Benny, sending you back there is the last thing I ever wanted to do.”

 

“I know. I know.” Benny shuffled his feet, kicking a some loose pebbles.

 

“-but my little brother is stuck down there.”

 

“This would be the little brother who wants to kill me, right?”

 

“You got access to the place.”

 

“By ‘access,’ you mean ‘getting beheaded’?”

 

He tried to think of a witty come back to that, try and lighten the mood, but he couldn’t do it. Hearing the words out loud shook what little confidence he had left. His voice began to shake. “Yeah, you're right... it's too much. It's not like I've exactly been there for you lately.”

 

Benny felt a pang of guilt. He knew this day would come, though he didn’t expect it under quite the same circumstances. If anyone had the right to send him back, it was Dean Winchester, the human that gave him a second chance, let him have his revenge.“What? Oh, come on, Dean. You know I love a challenge.”

 

“You're serious?”

 

“Hey, he's your brother. I say let's do this.”

 

“I owe you.”

 

“Oh, you don't owe me nothing. Truth is, uh... I could use a break from all this.”

 

“Its really been that tough?”

 

“I'm not a good fit, Dean. Not with vampires and, for sure, not with the humans. I don't belong. And after a while... that starts to wear on you.” He stopped, unable to make eye contact anymore. “Right? Cry me a river. Like you need to listen to this.”

 

“Well, when you get back up here, we're gonna fix all that, okay?”

 

“When I get back?”

 

“Yeah, you find the portal, and you’ll ride out of Purgatory with Sam just like you did with me, okay? As soon as I send you back, I'm gonna haul my ass up to Maine, and I'm gonna be waiting there for you when you get topside.”

 

Well damn. He was going to ask about the exit plan, but wonder of wonders, he wanted Benny back too. “Yeah. That sounds like a plan, chief. Let's get on with it.”

 

“You sure about this?”

 

“Not my first rodeo, man.”

 

Dean pulled a machete out through the impala’s window. He stood there, holding with a loose grip, as though he were hoping it simply fall away and be lost. With his free hand, he clasped hand with Benny, and was pulled into a tight hug. He had a weird feeling though, like he’d missed something important.

 

“Thank you.”

 

They pulled apart, but Dean hadn’t moved. He stood limp, waiting for someone to come along and stop him. Anyone. Was it so bad to ask for a miracle every now and then?

 

“Well, come on. You a wimp?”

 

\---

 

It seemed like the logical thing to do would be get to higher ground, maybe a tree. It would have been a nice idea, except when Sam looked around, the “trees” were maddeningly high, some to the point where they simply faded into darkness, their tops impossible to see. Those that didn’t extend into the skyline or were impossible to reach were already preoccupied with smaller, yet no less threatening looking monsters, watching curiously from above. Sam wondered why he hadn’t seen them before. Maybe they’d come waiting for something bigger to finish him off.

 

Instead he and Bobby found themselves wandering in a circle around where Ajay had dumped him. It had been another 5 day since exiting Hell, and so far nothing had come for them.

 

“I’m worried about _you_ , boy. I mean, this is paradise compared to Hell,” Bobby had reassured. “So you don’t gotta worry about me.”

 

Sam had tried to drink the water, finding himself very thirsty as compared to Hell, where he’d felt nothing in particular. The water, like everything else, was only like it’s earthly counterpart in looks. It had no temperature. It didn’t reflect light like it should have. It didn’t have any weight. He’d cupped his hands to bring it to his lips but the water went on flowing like it was still in the river, and slipped straight out of his hands. He lowered his whole head to dip into the water, and this time acted like he was not even there. He didn’t even get wet.

 

“God Bobby, how are you able to just wander around like that?” Sam asked, leaning against some rocks, still famished.

 

“I’m dead. I havent been hungry in years. Doesn’t feel much different here than before, appetite wise, anyway,” he shrugged.

 

After nearly a week without anything, he concluded that a lack of food or drink wouldn’t kill him. It would just be very, very painful.

 

“I can’t believe Dean spent a year in this place,” Bobby said eventually.

 

“Running and fighting, all day every day.”

 

“Must of been hell tryin’ to get him out of here.”

 

“I wouldn’t know, I guess.”

 

“You didn’t even _try_?”

 

Sam was quiet.

 

“Sam, what the-”

 

“Look, Bobby, Dean and I had an agreement, okay? If one of us dies, move on with our lives.”

 

“I know that agreement. I taught you that agreement. That's a _non_ -agreement.”

 

“Well what was I suppose to do? I didn’t know whether he was alive or not. He and Cas just fucking disappeared with Dick. I didn’t know where they were!” He wanted to yell. What right did Bobby have? “All I had was Crowley's parting speech saying that I was ‘truly alone’. He took Kevin and Meg. I had _no one_. No idea what to do or where to go from there. So I hauled ass before the leviathan could swarm, and I drove until I fell asleep at the wheel.”

 

“You weren’t trying to-”

 

“No. Well, maybe. But I wasn't going to stop, either,” he said bitterly.

 

“It’s alright, Sam.” Bobby put his hand on Sam’s shoulder.

 

\---

 

Getting back to Purgatory was disorienting, to say the least. Benny immediately reached for his neck. Head sitting on top, like nothing had happened. Amazingly, he even recognized where he was. It was where he’d been dropped off the last time he’d died, straight in the middle of vampire territory.

 

There was a nest of vampires, some he recognized, some he didn’t, that he’d been tracking for the last several days. Word spread fast that another stupid human had wandered in, and they weren’t going to let it get away like the last one.

 

“Word is that it’s another Winchester.”

 

“It’s like after Eve left, anyone thinks they can just wander in and out of here. I’m going to bleed it dry. Been too long since I last had a good meal.”

 

“I just want whoever it is out. How am I suppose to enjoy this crapsack afterlife if I still have to deal with hunters?”

 

At the very least, they seemed to know where they were headed, and only stopped when confronted by non-vampiric monsters.

 

The closer they got, the more of a pull Benny felt. Like when he’d found Dean before, it was as though a small signal went out to everything around that something was here that should not be. It was less strong without the angel, but it was enough.

 

It was too late to try and get ahead of them though, without risking being spotted. With so few hiding spots and little trust, the element of surprise was not something he was willing to give up just yet. When they finally found the humans, tired and exposed, he had to act quicker than he thought.

 

He had just finished ripping out an old acquaintance's throat, when he found himself under a the point of a crude blade by a human he didn’t recognize.

 

“Bobby no, wait!” Sam pulled the other man away and took the weapon into his own hands. “What are you doing here?” he gasped.

 

Benny gave a toothy smile, fangs still out and covered in blood. “Dean sent me.”

 

“Dean? Not my Dean,” Bobby said angrily.

 

“It’s fine, Bobby. He’s a buddy of Dean’s.”

 

“... a buddy?”

 

“A _good_ buddy,” Benny corrected.

  
“Jesus. How long have I been gone?”

**Notes for the Chapter:**

> Next chapter really will be the last one FOR SURE. I won't put a date though because I never follow my own deadlines lbr here.
> 
> Please alert me to any grammar/spelling mistakes thank.


	7. The Part Where He Kills Us

**Summary for the Chapter:**

> Benny, Bobby, and Sam make their way out of Purgatory while Dean muses over his own brush with Hell. The end is near, and some fates just can't be avoided.

**Notes for the Chapter:**

> Warning for more headcanons, overly affectionate hugs, angsty flashbacks, and naive descriptions of places I've never been to.

Dean tried not to think about a lot of things. Embarrassing hookups, painful injuries, Hell…

 

But when he had too much time to himself, like camping out in the middle of a forest in Maine for example, it was hard not to.

 

For over a week now he’d been parked in the Park Service campground, watching families, scout troops, or giggling teenagers with packs of beer come and go. The spot where he’d come out of Purgatory was a little less than a mile in, but the main road was a good 11 miles out, which was 11 miles too far in case he saw even the briefest flash of light. The welcome center did at least have a communal shower in the bathrooms, so despite the fact that he’d been living off vending machine food for 8 days, he’d lived through worse.

 

He thought about Heaven and Hell, Earth and Purgatory, or how he’d spent more time in Hell then he had even been alive. Over half his existence had been spent in that miserable place.

 

Even after he’d agreed to torture others so he could end his own suffering, the pain never really ended, Alistair made sure of that. Dean rarely ever left Alistair’s compound, a small peninsula surrounded by hideous blood river called Phlegethon.

 

“You know,” he had said one day, “we rarely name things down here in Hell. After all, the appearance changes based on whims of whoever has the power to do so. But after Dante came along, certain names just stuck.”

 

He shoved a very long, flexible needle into Dean’s jugular. He would have screamed as a very painful and thick fluid ( _some kind chemical cleaner humans use; I thought it might match well with your current case of liquefactive necrosis you’ve got going on in your lungs right now_ ) was pumped into his veins, if his vocal cords and tongue hadn't already been removed for the day.

 

“I don’t know how that guy got a peek at Hell. I certainly would’ve remembered if some pasty human was wandering around in my domain. He wasn't a prophet, so no heavenly help I suppose…” he mused. “Of course, he got a lot wrong too. Maybe he was just a crappy psychic, or uh, a good guesser. Well, whatever, right? He gave us some great names for places. As much as I hate that cold wasteland of earth, I’ll admit, there is some pretty good entertainment.”

 

There was no pain threshold, no passing out. Dean would  close his eyes (if he could) and try to remember being alive, even not-so-great memories. Anything and everything was worth remembering. It was the only thing that kept him from saying yes for three decades. It was only after a truly horrific day with Alastair, and realizing he could no longer remember what even Sam looked like, that he had finally given in. But the history lessons never stopped. Though the demon never said anything, Dean suspected it was to further drive out any of his human memories, to make it easier to forget he was anything but the creature he had become: a scorched, disgusting excuse for a human soul, but not quite tainted enough for Hell.

 

He didn’t know how he came back as he did. Even with his rebuilt body, Dean should have been able to barely remember Earth. He shouldn’t have had his same taste in food, music, sex partners- yet comparatively, his personality had hardly changed. It had to be something to do with how Cas had brought him back. For the couple of weeks or so, Hell was a non-existent memory, only slowly seeping back into memory as he slept.

 

He couldn’t even remember being pulled out the angel. His last day in Hell had wrought with a kind of anxiety he had never experienced. He had been working on a man who, in life, had been an accomplished botanist, but had sold his soul for revenge against his academic superiors. Just what they had done and why it was worth the man’s soul was something Dean hadn’t cared to find out. Alastair had been breathing down his neck for weeks, punishing Dean in front of his own projects.

 

“You are not leaving this room until you have become a full fledged demon, you stupid pile of shit. You’ve got the techniques down to an art, so _why are you still human? What is holding you back_?” he had screeched.

 

“Aw, something got your dick in a knot, sweetheart?” he rasped, aspirating on the blood leaking into his lungs. The beatings might as well have been a massage compared to what he’d gone through already. If this was the only punishment he got, back talk was more than worth it.

 

Alastair threw him to the ground. “Hell has been invaded.”

 

Dean laughed for the first time in a decade. “By _who_?”

 

“It’s none of your business who,” he snapped. “But I will tell you this: if they catch you, they will destroy you. And not in the nice way I do, where you get to come back all pretty. I mean permanently.”

 

“Is that suppose to scare me? Sounds like a good deal. Call your buddies over, we’ll have a party.” Dean smiled and turned his attention back to what was left of the man strapped to the table, trying to yell for all his worth with no lower jaw.

 

“You say that, but I bet I’ll find you days from now cowering in a corner from those filthy holy roller pigeons out there.”

 

“Aw, you _do_ care.” Dean pulled out a jug of some molten concoction and poured in on the victim's chest, leaving the crude shape of a flower in blackened, bubbling skin.

 

“They can’t just come down here, take away my best work…” Alastair mumbled.

 

Dean was broken out of his daze by a knock on the Impala’s window.

 

“Excuse me sir, are you okay?”

 

Dean opened his eyes. A late twenty-something guy with a slightly too large park ranger uniform and cornrows tied neatly together at the ends with a green hair tie was bent over and looking at Dean with a face of concern.

 

“Sorry ranger. Can I help you?”

 

“You just looked awful pale and dazed a minute ago. I thought you might have had like, a seizure or something.”

 

“Nah, I’m just… just a little tired.”

 

“Well see, that’s another thing. I can’t help notice you’ve been sitting here a while and-”

 

Dean held up his FBI badge without breaking his gaze towards the woods. “I’m on a stakeout, kid. Just let me know if you see any quick flashes of light about a mile out, okay?”

“Lights…?”

 

“Possible illegal explosives trade. I don’t need to tell you how dangerous that is. Get going before you blow my cover,” he barked.

 

The ranger awkwardly saluted and ran off back towards the park center. It was dusk now, and as much as Dean waned his brother back, he hoped that it would happen either in the next five minutes or wait until morning. Running through the woods nearly defenseless was not something he was eager to get back to.

 

He’d buried Benny in the cemetery of an abandoned church. The church itself had, ironically, been a vamp nest that was wiped out by Daniel Elkins nearly 50 years ago, and was tagged in his dad’s journal. He picked the spot because it was on the way and easy to find, but it also appropriate, in a weird way. Besides, it wasn't like he’d be buried there forever. Dean just had to put it somewhere to keep it from rotting away in the impala, or risk a cop finding it.

 

This whole trials thing was just one mess after another. It felt harder than it should be, for one. Not like a “too much research and heavy lifting” kind of hard, because that was pretty much to be expected. It was the sacrifice, the emotional toll of having to tell himself that it wasn't a choice of whether or not to do them and close Hell. Like he shouldn’t be feeling conflicted about risking his and Sam’s life for this, because it’s the right thing to do.

 

Telling Sam he had to say yes to Lucifer almost seems like it was easier. With that, the whole world was gone. With the Hell gates? The only people who would know were him, Kevin, and Sam. Maybe Naomi and her cronies. But the world would continue on. There was nothing but his own guilt at non-action and Sam’s insistence, yet Dean was beginning to feel like it simply wasn't enough anymore.

 

\---

 

“Ah Purgatory, I almost missed it here.” Benny held his foot against the corpse of a particularly large and ugly monster and heaved his whole body to wrench the weapon out of it’s back.

 

“Chupacabra don’t exist, dumbass. It’s gotta be something else,” said Bobby, kicking at the monster’s side with his foot.

 

“Well I don’t know what to tell you old man, it’s right here in front of you. I would think I should be the expert here, not you.”

 

“I’d say I _am_ some kind of expert. Now I’ve killed oni that look like this, but never have I found evidence of chupacabra.”

Benny jerked his body in a way that looked like he was using all his strength to hold himself back from getting into a fist fight. Sam put his hand on Bobby’s shoulder and motioned for them to start moving.

 

“Hey, Benny, listen,” Sam started after a few minutes. “I know you saved my brother's ass a few times down here, and I respect that.”

 

Benny rolled his eyes. “Yeah, and now I'm trying to save yours. You know, I'm a disgrace to my own people.”

 

“Yeah, I know… Look I owe you a lot when we get back. So, if you’ll let me, I’d like to start over.”

 

Benny shrugged. “Lets just make it to the home stretch for now. It’s maybe another 20 minutes from here, assuming we aren’t interrupted. Just tell grandpa over there to keep his cool until then.”

 

“I’m dead, not deaf.  I can hear everything you’ve said.”

 

It hadn't taken long until they found the clearing, in the middle of which was a rather dramatic looking cliff, and at the top where there was a vibrant blue crack, easily standing out against the watery-grey sky.

 

“There she is. You boys remember what I told you?”

 

Sam pulled out the knife. “Yeah. All right, Bobby, here it goes. When we get to earth and I release you, it's an express straight to heaven. No time for goodbyes.”

 

“Already said goodbye to you once, Sam. Didn't seem to take. No reason to think I won't see you.”

 

He wanted to say something, but despite all the time from the past few months he still hadn’t prepared anything to say to Bobby. It was hard enough the first time.

 

Bobby took the knife from Sam and cut his forearm. “But if they give me a rocking chair up there, I'm raising hell.”

 

He gave a kind of quick and pained laugh, before taking the knife back, slicing into his own forearm. “Conjuncti sumus, unum sumus.”

 

They clasped hand in a tight grip as Bobby’s image melted away. Sam’s arm dully glowed a pinkish orange color. It slowly faded, leaving behind a maddening itch.

 

“Alright, your turn.” Sam held the hilt towards Benny, who didn’t move. “Come on man, hurry up.”

 

“Sam, I-”

 

“Benny! It’s been a while.”

 

They turned to see at least ten very bloody, very agitated vampires making their way towards them, fangs bared and weapons drawn in front of them. It was on the other side of the clearing

 

“Still working with the Winchesters, I see. That’s a bad habit, that is.”

 

“Benny,” Sam said, panic seeping to the edges of his voice. “Jesus, hurry up. I can outrun them from here, just come on!” He shook the knife in his hand.

 

Benny made a smaller whimpering sound. Sam wasn't even sure he had actually heard it. Benny gently patted Sam’s back and began walking towards the others.

 

“It’s time for you to go Sam.”

 

“W-wait, what? Benny-”

 

“Go on. It's me they want.” He waved him on. “Go on. You just make sure you tell Dean I said goodbye.” His throat was thick and was hard to talk without a sob accompanying it. “I was never any good up there anyway.”

 

The vampire leading the group let out a spine chilling screech, sending all smaller creatures that had been lurking about to scatter in a hurry.

 

Sam took off towards the cliff, stumbling over a few rocks and bones that littered the ground. At the top (which seemed much lower from here than it did at ground level) the vampire nest has closed the distance with Benny who had already managed to snap one’s neck, and was trying to detach another’s fangs from his shoulder.

 

“Benny!”

 

Sam aimed his purgatory weapon at the vampire on Benny, sending it splattering into it’s back with a crack and squelch that was audible even from where he stood. Without missing a beat, he tore it out and lobbed off the head of another vampire running at him, just before the rest tackled him to the ground until he was no longer visible.

 

“Benny? Benny!” he yelled. Before he could move another inch, he felt a gentle pull at his side, and fell through the portal, the washed out grey of Purgatory falling away to an unearthly blue.

\---

 

Sam shook his cell phone and sighed. He’d forgotten he had it with him the whole time, but really it had probably stopped working ages ago. Even the hands on his watch had stopped. He estimated it had been about an hour now, sitting against the same tree without moving. He had watched the moon crawl across the sky, and he never thought he could miss what would normally be an afterthought, like the night sky, or temperature. There had been a tightly wrapped bag of food and drinks hanging from one branches, with a note from Dean.

 

Sammy, I think this is about where I popped out so I’m assuming it’s where you will too. If it is, I’ll try to hike out to you within the hour. DON’T DO ANYTHING UNTIL I GET THERE. JUST SIT DOWN AND EAT THE PROTEIN BARS.

 

                                             -Dean

 

“Sammy!” he finally heard in distance.

 

“Dean!”

 

He saw Dean about 50 meters out, waving and smiling. He looked tired, but still happier than he’d seen him in a long time.

 

“Just hold on, I’ll be over in a sec,” he shouted back.

 

Though he’d never admit it, Dean had always been a very physically affectionate and emotional person. He cried more, laughed more, hugged more, and this was no exception. He nearly knocked the wind out of Sam in a running embrace when he finally reached him.

 

“Purgatory, right? A real garden spot, ain't it? Jesus man, I thought I was never going to see you again.”

 

“Nah, I’d have found a way out eventually.”

 

“So how’d it go?”

 

“I uh- well there’s good new and bad news.”

 

“Uh oh.”

 

“Good new is, I got Bobby,” he said holding up his arm. “The bad news is that Benny… didn’t quite… make it back with us.”

 

“What?” he asked quietly.

 

“Dean, look- Benny, uh... He got us out. A bunch of vamps showed, and he used himself as bait. I get the feeling that even if that didn't happen, he didn't want to come back, you know?”

 

Dean didn’t say anything, but looked down at his feet and shoved his hands in his pockets.

 

“I’m sorry, Dean.”

 

“No, no. You’re probably right. I just- how did Bobby hold up?”

 

“He’s surprisingly good, considering. Ornery as fuck though. He kept picking fights the whole way back.”

 

“As he should be. Let's put that old man where he belongs.” Dean looked back up, grinning from ear to ear.

 

Sam pulled his sleeve back up, chanting as he sliced a shallow cut along his forearm.  “Solvo haec phantasmata in terram, et inde ad olympum.”

 

A stunning and bright translucent blue light burst skywards. It was hard to look at, like an uncovered lightbulb, but Sam could still easily classify it as one of the most beautiful things he’d ever seen. It circled the treeline a few times before ascending higher, when it was cut off by a deeply contrast red cloud of smoke.

 

“Well well well, Bobby Singer. I’d recognize you anywhere.” He looked back to the brothers. “Hello boys.”

 

“Let him go Crowley! He doesn’t belong in Hell!” threatened Dean.

 

“He does if I say he does. He's inflicted untold damage on my kind. From where I sit, actually, Hell's too good for him.”

 

“You slimey-” Dean started. Crowley flicked his hand and sent them both flying against the nearest tree. They grabbed at the invisible hands over their throats, gasping for air,  feet dangling as Crowley held them in place.

 

“Really boys? I would’ve thought you’d learn by now. Of course, I don’t know what I was expecting from Dumb and Dumber.”

Visibly straining, Sam turned his head towards Bobby’s soul, which had suddenly escaped in a beam of light.

 

“What! Come on, now what the hell was that? What did you you two do?”

 

“Put them down Crowley.”

 

They fell to the ground hunched over as gasping for breath when Naomi appeared, back to them and staring down Crowley.

 

“Let me see if I've interpreted the situation correctly. The Winchesters have freed an innocent from Hell, to which you are wrongfully trying to return it.”

 

“Siding with them, Naomi? You don't know those two. Before they're done, we'll both be locked away.”

 

“I'm just hoping they lock you away, dear. I’ll figure the rest out.”

 

“Bureaucrat,” he mumbled. “You're fighting outside your weight class.”

 

“Don't call me a bureaucrat,” she demanded angrily. She raised her hand, glowing with heavenly light. Crowley scowled and disappeared soundlessly. SHe smoothed out her skirt and fixed her bun, waiting for them to get up. Dean looked at her with a face of disbelief, and she smiled.

 

“I told you you could trust me, Dean.”

 

“Thanks for the help, I guess. But don’t think this changes anything.”

 

“Oh Dean. I don’t know how many times I have to tell you this, but I want to help Castiel. He is my brother, and he is your… _friend_. There will come a day when we can both do what’s best for him, and I hope that I can call upon you as an ally then. For all our sakes.”

 

Before he could respond she fluttered off, leaving them alone in the darkness of woods.

 

“What the hell was that about?” Sam asked.

 

“I'll tell you later. Let's get this trial done.”

 

“Kah-nuh-ahm-dahr.” Sam groaned in agony, falling back to the ground and grasping his arm as it glowed a sickly color.

 

“Sam? What? What?! Talk to me! What?!”

 

He gasped, grimacing and taking deep gulps of air. “It's okay! It's okay! It's okay. I'm fine. It's done. It's done.”

 

“Are you sure?”

 

“Yeah, yeah, lets just go,” he said weakly. “I haven’t showered or had a decent meal in months. Lets just get back to the bunker.

 

Dean put his arm under Sam’s shoulder and helped him up. Sam moaned and leaned tiredly against Dean.

 

“Come on little brother. I passed a Biggersons on the way up here. It’s our favorite restaurant after all.”

 

“Oh my god, shut _up_.”

 

**Notes for the Chapter:**

> I have never been to Maine. I have no fucking idea what the 100 Mile Trail or Baxter State Park or whatever looks like or if they even have a visitors center. I've only ever been to parks in Maryland, which are all kick ass and have nice welcome centers, gift shops, cute park guides who hold birds on their arm, and communal showers. So if you've ever been to where Supernatural pretends to be set in during this episode, sorry for the inaccuracy! On a side note, you should all come to Maryland. We've got crab cakes and ponies and horses and same-sex marriage and horses and murder. Best place ever.
> 
> I didn't include the last few scenes with Kevin and talking about feelings in the Impala, because that was one of the few parts they got right in the episode and there wasn't much to left to add.
> 
> Thanks for being patient over the entire stupid year it took me to finish this! Just because I kept forgetting about and/or being too busy to write doesn't mean I didn't love every minute (◕‿◕✿)
> 
> As usual, let me know of any grammar/spelling mistakes in the comments.

**Author's Note:**

> Thanks for reading, or bothering to skip down the page to read this, anyway. Overall, I'm not going the lie, the episode made me very conflicted. The acting was great, I liked the twist of Purgatory and the idea of rouge reapers, but I feel like it should have spanned 2 or even three episodes. There just wasn't enough time to explain everything properly, and too many holes were blown into the show's established mythology for me to feel comfortable with. So, you have before you my attempt to rationalize everything. I hope you enjoy it.


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